Journal of the American Chemical Society, volume 130, issue 44, pages 14891-14899
Enantioselective Iridium-Catalyzed Carbonyl Allylation from the Alcohol or Aldehyde Oxidation Level via Transfer Hydrogenative Coupling of Allyl Acetate: Departure from Chirally Modified Allyl Metal Reagents in Carbonyl Addition
Publication type: Journal Article
Publication date: 2008-10-08
Quartile SCImago
Q1
Quartile WOS
Q1
Impact factor: 15
ISSN: 00027863, 15205126
General Chemistry
Catalysis
Biochemistry
Colloid and Surface Chemistry
Abstract
Under the conditions of transfer hydrogenation employing an iridium catalyst generated in situ from [Ir(cod)Cl]2, chiral phosphine ligand (R)-BINAP or (R)-Cl,MeO-BIPHEP, and m-nitrobenzoic acid, allyl acetate couples to allylic alcohols 1a−c, aliphatic alcohols 1d−l, and benzylic alcohols 1m−u to furnish products of carbonyl allylation 3a−u with exceptional levels of asymmetric induction. The very same set of optically enriched carbonyl allylation products 3a−u are accessible from enals 2a−c, aliphatic aldehydes 2d−l, and aryl aldehydes 2m−u, using iridium catalysts ligated by (−)-TMBTP or (R)-Cl,MeO-BIPHEP under identical conditions, but employing isopropanol as a hydrogen donor. A catalytically active cyclometallated complex V, which arises upon ortho-C−H insertion of iridium onto m-nitrobenzoic acid, was characterized by single-crystal X-ray diffraction. The results of isotopic labeling are consistent with intervention of symmetric iridium π-allyl intermediates or rapid interconversion of σ-allyl haptomers through the agency of a symmetric π-allyl. Competition experiments demonstrate rapid and reversible hydrogenation−dehydrogenation of the carbonyl partner in advance of C−C coupling. However, the coupling products, which are homoallylic alcohols, experience very little erosion of optical purity by way of redox equilibration under the coupling conditions, although isopropanol, a secondary alcohol, may serve as terminal reductant. A plausible catalytic mechanism accounting for these observations is proposed, along with a stereochemical model that accounts for the observed sense of absolute stereoinduction. This protocol for asymmetric carbonyl allylation transcends the barriers imposed by oxidation level and the use of preformed allyl metal reagents.
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Citations by publishers
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- We do not take into account publications without a DOI.
- Statistics recalculated only for publications connected to researchers, organizations and labs registered on the platform.
- Statistics recalculated weekly.
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Kim I. S., Ngai M. Yu., Krische M. J. Enantioselective Iridium-Catalyzed Carbonyl Allylation from the Alcohol or Aldehyde Oxidation Level via Transfer Hydrogenative Coupling of Allyl Acetate: Departure from Chirally Modified Allyl Metal Reagents in Carbonyl Addition // Journal of the American Chemical Society. 2008. Vol. 130. No. 44. pp. 14891-14899.
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Kim I. S., Ngai M. Yu., Krische M. J. Enantioselective Iridium-Catalyzed Carbonyl Allylation from the Alcohol or Aldehyde Oxidation Level via Transfer Hydrogenative Coupling of Allyl Acetate: Departure from Chirally Modified Allyl Metal Reagents in Carbonyl Addition // Journal of the American Chemical Society. 2008. Vol. 130. No. 44. pp. 14891-14899.
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TY - JOUR
DO - 10.1021/ja805722e
UR - https://doi.org/10.1021/ja805722e
TI - Enantioselective Iridium-Catalyzed Carbonyl Allylation from the Alcohol or Aldehyde Oxidation Level via Transfer Hydrogenative Coupling of Allyl Acetate: Departure from Chirally Modified Allyl Metal Reagents in Carbonyl Addition
T2 - Journal of the American Chemical Society
AU - Kim, In Su
AU - Ngai, Ming Yu
AU - Krische, Michael J
PY - 2008
DA - 2008/10/08 00:00:00
PB - American Chemical Society (ACS)
SP - 14891-14899
IS - 44
VL - 130
SN - 0002-7863
SN - 1520-5126
ER -
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@article{2008_Kim,
author = {In Su Kim and Ming Yu Ngai and Michael J Krische},
title = {Enantioselective Iridium-Catalyzed Carbonyl Allylation from the Alcohol or Aldehyde Oxidation Level via Transfer Hydrogenative Coupling of Allyl Acetate: Departure from Chirally Modified Allyl Metal Reagents in Carbonyl Addition},
journal = {Journal of the American Chemical Society},
year = {2008},
volume = {130},
publisher = {American Chemical Society (ACS)},
month = {oct},
url = {https://doi.org/10.1021/ja805722e},
number = {44},
pages = {14891--14899},
doi = {10.1021/ja805722e}
}
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Kim, In Su, et al. “Enantioselective Iridium-Catalyzed Carbonyl Allylation from the Alcohol or Aldehyde Oxidation Level via Transfer Hydrogenative Coupling of Allyl Acetate: Departure from Chirally Modified Allyl Metal Reagents in Carbonyl Addition.” Journal of the American Chemical Society, vol. 130, no. 44, Oct. 2008, pp. 14891-14899. https://doi.org/10.1021/ja805722e.